Episode 430 and today’s guest is Phil Beauregard, Managing Partner of Impellent Ventures.
I first met Phil back when Boston was going through another massive resurgence of growth following the financial crisis of 2008. It was a special time when local founders and investors banded together to help build and scale the Boston tech ecosystem. It was a movement that is reminiscent of what we are seeing today with the Mass AI Coalition. There was a major buzz in the air back then, and it worked, resulting in the launch of multiple successful companies, including two of Phil’s own startups which were both acquired.
There is a phrase that Phil commonly uses, which is “why join the Navy when you can be a pirate,” and I think it speaks volumes to his mentality and how they deploy capital at Impellent Ventures.
They simply don’t follow the herd, especially when it comes to finding elite entrepreneurs. They are entirely location-agnostic and welcome working with exceptional founders who are tackling massive, real-world problems in emerging ecosystems… not just out in Silicon Valley.
Impellent Ventures is focused on making seed and pre-seed investments. The firm is led by Phil, David Brown (who previously appeared on Episode 190), and Tariq Trotter, aka Black Thought of The Roots, who serves as a General Partner at the firm.
In this episode of our podcast, we cover:
- A conversation around building startups outside of San Francisco, and why we are living through the “consumerization of the enterprise” era.
- The correlation between smaller fund sizes and investor returns.
- Phil’s background growing up in New Bedford and studying business at The Wharton School at UPenn, plus how he first caught the entrepreneurial bug and met his co-founder, Matt Grace.
- The inside story behind his two exits: Objective Logistics to Carbon Black and Rekindle to HubSpot.
- His transition from operator to investor at Impellent Ventures, plus all the details on their unique investment criteria, portfolio company examples, and how Tariq Trotter joined the firm.
- His role as an early advisor to multiple successful tech companies, including the critical advice that Toast luckily chose not to take.
- How Phil is leveraging AI to build his own Relationship Intelligence System, helping him scale his ability to “pay it forward” to the ecosystem.
- Plus, so much more!
Transcript
Keith Cline (02:37)
Phil, thanks so much for joining us.
Phil Beauregard (02:39)
Thank you for having me.
Keith Cline (02:42)
feel like this is overdue. This is one of these conversations that I’m like, how have we not had this podcast conversation being that I’m over 420 episodes into this thing and your partner David Brown was episode 190. So maybe we just had to spread it out a little bit, but I’m excited to finally have this conversation to, we’re gonna talk a lot about a lot of stuff here. So hope you’re ready.
Phil Beauregard (03:04)
Cool, I’m ready. Yeah, I think 425 sounds right. Like I’m kind of like the C student, you know? Right at the side of the normal curve, not like a standard deviation away from cool, but like kind of getting there. So I feel like that’s the right place, you know? So that’s cool.
Keith Cline (03:13)
Right.
Right?
Okay, we need to talk about something that, know, Boston’s having another like moment. There’s the mass AI coalition. There’s this buzz of, hey, great companies can be built in Boston. You don’t have to go to San Francisco. So you run a fund that actually funds a lot of companies that are, you know, not just Boston, but elsewhere and not like major tech hubs sometimes. So I guess I wanted to get your point of view of why is it a good thing to build outside of San Francisco.
Phil Beauregard (03:58)
necessarily think that the whole idea is to relegate San Francisco into this kind of pejorative slash, what’s the opposite of a dunce cap, right? Like, I mean, San Francisco is the most startup and innovation dense geography filled with all these amazing people in the entire world. I I don’t think anybody denies that. We certainly don’t. I mean, we’d be total dolts if that were the case. I think that really what it comes down to is that we lean into the concept that genius, IQ, grit, maybe even more grit, ⁓ and all of these qualities that can make for people that start…companies and build products and have ideas is evenly distributed across zip codes, but capital and good mentorship in the things that come with density are not. ⁓ So what does that all mean? That means that if you’re familiar with the concept of estuaries ⁓ or places where there are breeding grounds and all of these things are just starting to pop up. ⁓ The little fish, right, that are about to go into the big ocean. I think the idea is to find and recognize those people as soon as humanly possible and surround them with love and mentorship and some capital, ⁓ institutional capital.
I don’t think it’s a new concept necessarily. I do think that the prosecution of the strategy is a particular bent that has been effective for us. And that comes from the days, and we can go into this a little bit later on, in teaching by the Jeff Fagnans of the world from when we were 26 years old. And the real idea is like, we will say it in Pellant, keep your hands busy.
And what does that mean? For us, it really means put our rucksacks over our shoulders, hop a commercial flight, you know, because our PJs are probably in service or something along those lines, or we’re in between our private jets over here. But yeah, get our asses on the budget airlines ⁓ and fly to where the entrepreneurs are and fly to where the influencers are and fly to where, you know, people are holding tremendous civic pride. And billionaires and centi-millionaires, they go back to Pittsburgh, they go back to Toronto Waterloo, they go back to Rochester, they go back to Philly, they go back to Austin, and they put their names on hospitals. Right? And they live there. And they want to see the environment pulsate. And so all of these things in the universities, they all combine.
Keith Cline (06:58)
Mm-hmm. Right.
Phil Beauregard (07:11)
to create an ample breeding ground for what goes into good entrepreneurship. It just so happens that if there aren’t support mechanisms like the downstream capital and the mentorship, they’re right from the get-go ⁓ in ample and quality, then those fish will immediately leave because they’re getting told to go to San Francisco immediately. Because that’s just such an un…
Keith Cline (07:36)
Right.
Phil Beauregard (07:39)
Relenting marketing machine on LinkedIn. are like when you’re talking about the Boston AI stuff, right? It’s I immediately nod my head because it’s just it’s it’s Honestly, it’s a coordinated campaign that I saw right from Will from WHOOP and Giuseppe from 186 and you know, all these different leaders, there and these are all friends. ⁓ And they did a great job of everybody just attacking it right away and saying, this is who we are. Let’s rally around it and let’s let’s let’s make this heard. And I think they did an awesome job of it. And that’s where it starts. It starts with that spark and it starts with attention and then a narrative forms. And so is it true? It just so happens that Boston has it’s not new. Some of the best universities and research labs and PhDs in science in the entire universe. mean, a lot of them, you know, walked their way over to San Francisco. We don’t need to mention all of their names that we got told growing up in Boston. Already left, and that’s why Boston’s so shitty, and you know, it’s a frontier market. And Puritanical and all that other stuff that the San Franciscans used to call us back in the day, and probably still do. ⁓ Yeah, I mean, it’s a place where greatness can happen.
I think the idea is, and where we really need to focus is to nurture that. And the question ends up being, how do we do that appropriately? And two main mechanisms there are capital, mentorship, relevant mentorship. Relevance is important, curated mentorship. Because if you have…people that haven’t been there done that or just for whatever reason aren’t necessarily capable of giving good advice to entrepreneurs at these critical periods. And I mean, when you’re that early, a critical period could be choosing the right bank or not taking venture debt or learning how to forecast your cash. That’s almost like the blind leading the blind. It’s almost like a, you know, physics professor trying to teach somebody about Shakespeare. Unless there’s some sort of amazing polymath. So long story short, that’s why we’re interested in these places.
And the way we think about that is to get on planes and meet people where they are because we do believe that face-to-face is important. We do believe that that enters into the equation. We do believe that that is part of the sales process to sign up great entrepreneurs and help them. And when we do so, hopefully we can make our small mark and start to create or help create some of these companies and aid them and abet them.
And if they want to go to San Francisco afterwards or one of these other places, I mean, they should a hundred percent, whatever, whatever works. So.
Keith Cline (10:43)
Yeah. I mean, like Boston, I mean, to your point with the Mass AI Coalition, like Ryan Durkin, like he is a force of nature. Like he had reached out to me, I don’t know, last October. It was like, hey, I’m thinking about doing this stuff. And I’m like, if there’s one person that can pull this off, it’s him. And he has gotten so many people and rallied the community together, which has been phenomenal. And Boston needed that because…
Phil Beauregard (10:50)
Hmm.
Keith Cline (11:10)
There’s all these success stories in Boston, people just don’t really talk about them. It’s very humble type of crowd, heads down, just keep building. So it’s good to celebrate once in a while.
Phil Beauregard (11:16)
You know, it’s really funny because first things first, addressing Ryan, like, I don’t know Ryan personally, ⁓ but I remember Chase Garbarino told me about Ryan, must’ve been a decade ago.
I just said, this guy is an absolute force. He’s the right person. I think we were discussing some other company or something like that. And that’s when he kind of came on my radar and then seeing what he’s done since, is… Yeah, no, so yeah, that’s precisely it, right? So that’s where I kind of knew that from. And yeah, the other funny part about it is it’s not necessarily…
Keith Cline (11:48)
He was part of the CampusLive crew, remember them? For us?
Phil Beauregard (12:05)
What the person is saying about themself. Because that just becomes, people just think that you’re not humble bragging or, people don’t wanna hear other people until they become kind of Elon Musk and even then it’s obnoxious, ⁓ talk about themselves and be like, I’m awesome, I’m awesome, I’m awesome, I’m awesome, right? But when everybody else says that person’s awesome, right? Then you start to say, whether I respect their opinion or not. mean, something’s going on over there, right? And so what San Francisco’s been fucking awesome at is everybody’s like, Bill Gurley is a god. Peter Thiel is the most fantastic person on earth. ⁓ Have you heard Peter Fenton talk? Those Sequoia guys, my God. Andreessen Horowitz, Andreessen Horowitz, Andreessen Horowitz, Andreessen Horowitz, Andreessen Horowitz. You know, like, you’re just fucking inundated with all of these names and these people and they become a pantheon. Right? And to a degree, sometimes it becomes a self-fulfilling prophecy. I mean, the human race and us as sapiens are so used to constructs. Right? And what I mean by that is that why the fuck do I need a Rolex watch?
Because everybody else is talking about it it looks cool and this, that, and other. It’s a piece of fucking metal on my wrist, dude. Like ⁓ anything can work, right? Why does the world need Andreessen Horowitz? Because everybody says it’s cool and it just keeps getting bigger, right? So other people talking about, Durkin’s really good at getting other people talking about this. And I think that this is where that sort of stuff starts.
Keith Cline (13:34)
Yeah.
Well, when I was preparing for this podcast, I was listening to another interview that you gave and I learned a fun fact. So is it true no VC fund greater than a hundred million dollars has generated a greater than a 5X return?
Phil Beauregard (14:09)
I was sense corrected on that. ⁓ And there’s one. yeah, I forgot who it was. It’s like one or two. Like, I’ll have to get back to you on it.
Keith Cline (14:18)
Okay, one, but still rare.
Phil Beauregard (14:25)
have to get back to you on, no, no, no, it’s beyond, this isn’t a counter to your point or to my point that you just referred to. Like,
Keith Cline (14:31)
No, no, it validates the fact that it’s just one.
Phil Beauregard (14:36)
The mere fact is, that like, it’s almost like the laws of physics apply and gravity applies to fund sizes in AUM, right? As it pertains to startups and VC. funds that are sub hundred million dollars, statistically, you know, are far more alpha oriented and can beat the three Xs so they can range up to, mean, think, I don’t know what founder collective one ended up being, but I think it’s 20 plus, right? ⁓ So yeah, so I mean, and those guys are our greatest mentors here. I used to say whether they know it or not, but Paley knows it at this point, because I won’t shut up about him. ⁓ He’s just…
Keith Cline (15:16)
Yeah, insane.
He’s amazing. He’s just extraordinary person who takes time. He’s so busy. Anytime I reach out to him, he’d be like, sure, let’s get on and count. Just, okay. Never me. It’s just amazing.
Phil Beauregard (15:45)
He surprised me and maybe that’s a backhanded compliment, but he surprised me at his openness and his willingness to help at the get-go when I first started. yeah, he’s been otherworldly. But those guys just deserve all the success that they have. And they’re very good at getting people to like them. And it’s intentional.
Like you can see the intent behind it. And it’s great. And they’re just super helpful. But yeah, so they deserve that 20X plus and all the other great things that they do. You don’t see that at the larger firms, right? Because at those stages, most people know this math, but when you have a billion dollar plus vehicle, nevermind 10 to 15 billion like Andreessen Horowitz.
It’s you have to move much, much larger checks. ⁓ and just the mere kind of like fact that when you’re moving a hundred million dollar checks instead of a million dollar checks or $50 million checks instead of $2 million checks, the outcome has to be that much bigger. And there’s only so much liquidity slash like ceiling in the entire industry to create multi trillion dollar outcomes to fulfill the entire need of that fund. Right. From a, from a return.
Do I think that that’s changing to a degree? think that, you know, people five years ago were like, there’s no such thing as a trillion dollar fucking company. Right? And it’s like, well, you know, strap, strap in and, know, into your seat belts and get ready for the ride because, know, crush your glass ceilings. Because now we are seeing a true…
Keith Cline (17:15)
Yeah, Well…
Phil Beauregard (17:31)
consumerization of the enterprise era where people that didn’t ever consider buying software to make their lives easier or enterprise software or creating their own agents, physicians, people that have never touched this stuff in their entire lives, individuals, contractors, they’re buying software. From Anthropic and from OpenAI and from all the app layer companies. So you’re seeing the true consumerization. And what does that mean? The total amount of money going into software is going up.
It’s not just your buyers at the little companies and other startups and Salesforce and like, you know, your typical accounting firms and so on and so forth. It’s literally your next door neighbor is buying Anthropic Claude Code is buying probably more often than not is buying an app player that’s helping out their business. And that is net new dollars into the ecosystem. And that’s why revenues will go up far past what they used to. And that’s why market caps will go up higher than that. Nevermind inflation. So.
Keith Cline (18:24)
Mm-hmm.
Mm-hmm.
Phil Beauregard (18:37)
I don’t even remember where we were, but I just wanted another other grant.
Keith Cline (18:41)
Well, let’s talk about your background story. So you grew up in New Bedford, right? How did you end up at Penn?
Phil Beauregard (18:46)
Quaint little city by the sea. How did I what?
Keith Cline (18:50)
Yeah, great place.
How’d you end up at Penn? You went to Wharton.
Phil Beauregard (18:56)
I went to my college consultant who was a consultant to, not college consultant, I’m sorry, guidance counselor. I just did college consultant. I just gave it a shine. ⁓ At New Bedford High School, so my graduating class was 4,000 people it started with. I think it ended up graduating like 2,900 or something. was a super high attrition rate.
Public high school, pretty rough. And the guidance counselor, my guidance counselor served 500 kids And so my short time in her office one day when I was a junior and she at the end of my junior year, she was saying, listen, like, what do you, we’ll talk about applying for colleges and this, that, and the other. And she said, what do you want to do? Like, what schools are you thinking about? And
I said, I don’t know, mean, the stock market was really up. My dad was a lawyer, so was like, maybe law, but I don’t think so. The stock market was up so high at that point. This was like 1999 or 1998 or something along those lines. Like we were on a little bull run. And I was just like, business? And she’s like, business, great, sounds good. Where do you wanna go then? I said, what are the top three business schools that do business. She essentially, truly, because at that point I was thinking about soccer and I don’t know, probably going on dates or something like that. So she ended up saying, well, she didn’t even get past Wharton. She literally was like, number one is Wharton at the University of Pennsylvania. I was like, I wanna go there.
Keith Cline (20:22)
You know, business.
Phil Beauregard (20:47)
And she was like, well, you should do these. I was like, I don’t want to go there. So, so ended up, ⁓ yeah, ended up making my way to Penn, not knowing my ass from my elbow. And, and, and to a degree, I still don’t, but, that’s, that’s how I chose Penn. and yeah, so that was the, the rest was, the rest was, was, was history. Let’s call it history.
Keith Cline (21:10)
From what I saw on your LinkedIn, you started out doing the investment banking thing, which is pretty typical, but did you always want to start your own company?
Phil Beauregard (21:18)
I had no idea what that meant. No, the answer is no. I think when I was a kid…
I remember wanting to be my own boss or having those inklings. And maybe that was just me being obstinate or maybe it actually was foreshadowing the type of person I was to become, right? Like somebody that’s a little bit, honestly, more of a pirate than a Navy man. And I remember…
Even in my management 101 class the first year at Wharton, the professor, this guy comes out and he’s a really smart guy. Obviously very bonafide, like all this tenured shit and so on and so forth, consultant to the stars, who knows. And he comes out and he says, if you want to be a CEO, here’s the track. And he put it up on a presentation and it was like.
Long story short, was like you have to do 20 years at a consulting company, then you have to go into like, you know, 10 years at the company and move your way up the ladder. And by the time that you’re 55 or 50, I think it was, you can first become a CEO of a company. And
Keith Cline (22:32)
you
Phil Beauregard (22:32)
You can imagine like my response now it’s like what the fuck but back then you nobody would nobody was thinking that like really thinking that way i mean the only entrepreneurial blogs out there were Mark Suster’s Fred Wilson’s the VentureHacks that then became Nivi Naval who just yeah yeah and Brad Feld that’s it nothing else can you imagine that entire linkedin
Keith Cline (22:46)
Mm-hmm.
Angelist.
Phil Beauregard (22:59)
universe filled with nothing but just LinkedIn was even LinkedIn. So I mean just those were the people that were talking about entrepreneurship. And so it was slim pickings. I mean they were good pickings but it slim pickings. And yeah so this guy was saying that and I was just like fuck that. You know I want to I want to be the CEO two years out of school. Now that’s a little asinine but long story short, know, did the investment banking thing. 2009 came rolling around. That situation figured itself out. And, you know, walked out with my proverbial box. And I had written, this sounds so much haughtier than it is in my mind. I had a notebook, a moleskin, and I had written some algorithms in it around, you know, how do I rank waiters, waitresses, and retail salespeople? And what if I reward them?
Keith Cline (23:31)
Mm-hmm.
Phil Beauregard (23:54)
with the shifts that they want.
Keith Cline (23:56)
Mm-hmm.
Phil Beauregard (23:58)
Creates this competition. Back then it was like microeconomic concepts of like deadweight loss and all this other stuff. it was a fascinating like and it actually was really I mean it was pressing and so I took that and I was like maybe I can do this company thing and I started working from a coffee shop and I had no idea what to do and had no idea I needed a technical co-founder I mean those terms weren’t even a thing like
Keith Cline (24:18)
You
Phil Beauregard (24:20)
And so, ⁓ two years later, it took two years of like just toiling away with, with no pay, and ended up getting funded by Jeff Fagnan and Rich Miner and Lee Hower three Boston greats. And that, that, that was, yeah, that was the start of my, ⁓ all still like, you know, amazing, amazing folks. And that was,
Keith Cline (24:34)
That’s a great roster right there.
Phil Beauregard (24:43)
know, definitely an inflection point in my career and kind of like my network in Boston and just kind of who I was.
Keith Cline (24:51)
How’d you meet Matt Grace, your co-founder?
Phil Beauregard (24:54)
He was a guy from Dartmouth, so we were from the same area. It was like literally two people. Everybody was just like, yeah, this guy. Thinks about starting companies and he is a software guy. ⁓ Again, not necessarily Palo Alto or anything like that, right? Like ⁓ New Bedford, Massachusetts and Dartmouth. So yeah, we just kind of came together as social circles and everything else like that and said, all right, let’s go mess around with this stuff.
Keith Cline (25:25)
Well, you ultimately created what you’re looking to do, right? So this was an old version of your website here, Objective Logistics, right?
Phil Beauregard (25:37)
Not the oldest, but that was one of the oldest, yeah, that was way back in the day. Yeah.
Keith Cline (25:40)
in one of the older versions.
And then, because you were doing from what I, because I remember the company, I remember, you like you guys raised, it was like a, ⁓ you guys were doing AI, weren’t you back then? Like machine learning kind of thing or?
Phil Beauregard (25:56)
It was,
it was, there was machine learning. It was back then, you know, we just, we went into POS systems and amassed data and then normalized data and then used the data and then automatically, you know, rostered employees. So sure. ⁓ I remember there was like big data, gamification, like they’re all different monikers that were attached to it. ⁓ But.
At the end of the day, was way, I truly can say it was way before, what is this way back machine? ⁓ It was way before its time. Yeah.
Keith Cline (26:27)
Totally. I mean, this is the version of your website that I totally remember. As soon as I saw this, I’m like, I remember the logo. I’m like, yep.
Phil Beauregard (26:33)
Dude, our first presentation was like a PowerPoint that was like 40 pages long and it’s quite frankly one of the most horrifying things that I’ve ever seen in my life. In fact, gives me night terrors to think about it. The logo was Times New Robin, objective logistics over a globe, a PowerPoint, Microsoft, Earth. It was pretty bad, it was pretty bad.
Keith Cline (26:48)
you
So you were, I think I saw your address. You were like the Kingston street, right?
Phil Beauregard (27:06)
Yeah, we ended up moving to, so we did a couple different things. We moved from, one of the things that Fagnan mandated, actually, in the term sheet, you know, off market terms, Jeff, ⁓ was that we had to move to Boston from New Bedford. And of course we were like, hell yeah, let’s go do it. So we ended up, we ended up illegally, I think we’re past the statute of limitations here, illegally getting an apartment at Binney Street in Cambridge.
And so was literally a two-bedroom apartment and we were working out of that. Like we would like sneak in like other people and like, you know, cause we weren’t supposed to have a workplace there. And there were a couple other companies over there. I don’t know if I want to out them. I guess again, ⁓ Crashlytics Wayne and those guys were there. then, yep. and Matt Bellows from Yesware was there and Lucky Labs, Noah was there. ⁓ So we were all in that same place in our own little apartments. And then.
Keith Cline (27:51)
No way.
Okay. Yep, yep, yep.
Phil Beauregard (28:06)
when we had to go legit, we went to one around Kingston. So yeah, that’s right.
Keith Cline (28:10)
But I just remember that building had a lot of great early stage companies too. Like Terrible Labs was in there too, weren’t they? In the Kingston street.
Phil Beauregard (28:16)
Yeah, terrible labs. was Matt, Steven Marcus and Matchbox. Steven’s over at a great venture firm now on the west coast named Riot Ventures that just did true anomalies most recent round. So yeah, there was some, there was some OG stuff going on. don’t remember. It was, I don’t remember if Promoboxx was there, but somebody, no, maybe not Promoboxx, but somebody else was there. Yeah. There were, there were.
Keith Cline (28:21)
box.
Maybe. I just remember,
I remember stopping by and just looking at the exterior Rolodex of companies and I was just like, oh my God, I know all these companies. This is so cool.
Phil Beauregard (28:47)
Yeah. So, so we, was a little, I, the rent was 20 bucks, 19 bucks a square foot to start. And it was when downtown crossing wasn’t really a thing. you know, we’re from New Bedford, so we can handle a couple, ⁓ miscreants, hanging around. So we, it looked dingy and stuff, but it was great. And then, that’s when downtown crossing started to, started to pick up a little bit.
And it was a cheaper And
Keith Cline (29:23)
Eventually the company was acquired by Bit9, which ultimately became Carbon Black, which was then acquired by VMware. So how did all that take place?
Phil Beauregard (29:31)
It was, we had had a…relatively substantially larger transaction that was that we thought was going to get closed with a different company and that company which was this huge strategic acquirer I Don’t say the name of it pulled their Pulled the transaction we had done all the meetings we’ve gone through all the diligence. We were literally at signing and They ended up pulling their their offer with I think we had three weeks of cash left
So it was brutal. ⁓ I mean, that was rough. That was hard. Like I talked to lot of entrepreneurs on a daily basis, obviously, and kind say like, what’s the hardest thing you’ve ever been through in your life? Or like, you know, we’ll ask certain questions. I wouldn’t say that’s one of the hardest things I’ve ever been through in my life, but I certainly would rank it top 10 of kind of like feeling like shititude type situation. ⁓
Keith Cline (30:07)
Wow.
Yeah.
Phil Beauregard (30:33)
And so after that, we ended up essentially, I don’t want to call it a kick save, but like we ended up talking to Patrick Morley and we had a crazy good team and you know, some great math and you know, some great tech and stuff like that. um, they were able to, to, you know, strategically utilize like, like what we had to offer. And so we ended up selling to them and they ended up going public, um, right, right afterwards. They had combined with carbon black and went public. So, um,
Keith Cline (31:01)
Mm-hmm.
Phil Beauregard (31:02)
Yeah, it was the best outcome we could get at the time. And certainly not what I had expected seven and a half years prior, especially as my great friends were about to take, or on the course to take companies public, like Jason from Draft Kings and all these different folks that were running these large Boston companies. these things happen.
We were, proud of what we ended up doing. And then there was rekindle too, which was a little bit smoother after about a year and half to HubSpot.
Keith Cline (31:38)
Well, so I wanted to talk about rekindle. So how was that born? Because it was during the same timeframe, right?
Phil Beauregard (31:43)
Yeah, so I had another idea. Those are the only two ideas that I’ve had in my entire existence. The idea stopped after that. I’m kind of not kidding. ⁓
Keith Cline (31:52)
But the rekindle idea is brilliant.
Phil Beauregard (31:56)
Yeah, Rekindle was really good. ⁓ And Miner, like the whole group of guys did the same thing. It was like this parallel entrepreneurship thing, where some people were like, you know, one CEO should not form two companies and like, they’re probably right. I mean, there’s been like one person that’s done it, right? Like Jack Dorsey. ⁓ two now, two now, Elon Musk. ⁓
Keith Cline (32:15)
Jack Dorsey,
Phil Beauregard (32:20)
And yeah, I didn’t end up having the experience, either of them obviously, but ⁓ yeah, Matt ended up going over to that. I put him in charge of rekindle him and a guy by the name of Mike Lisovich, who’s now, he was high up at Cargurus. I don’t know where he’s at right now. ⁓ he’s at Klaviyo now. ⁓
And yeah, just good crew and we were building, it was really a relationship graph. And what I mean by that is that it was, what people are still trying to do is just like, but this is back when LinkedIn and Facebook’s APIs weren’t deprecated to the point that they are. And you could really get information on how people are connected via those two APIs and then phone numbers. And so we built this really complex, like very quickly relationship graph. And by the time that I had sold Objective Logistics, I was torched. And we had the opportunity to sell it to HubSpot. I needed a bath at that point.
We could have gone to San Francisco and like raised and so HubSpot ended up using it to power Sidekick, which then became their CRM. So yeah, it was a great, it was fun. was fun. So yeah.
Keith Cline (33:22)
Mm-hmm.
Right.
and it was HubSpot’s first acquisition post-IPO.
Phil Beauregard (33:40)
Yeah, that’s right, that’s right. And it made the stock jump. I remember that was really funny because the amount that the market cap jump that occurred because they announced that like it was way overblown, like meaning it shouldn’t have caused that much fervor. And I remember we were like, holy shit, we should ask for more, right? Like.
Keith Cline (34:02)
Hahaha
Phil Beauregard (34:03)
They got a crazy good deal on this one based on what happened here. but yeah, it was just a little tucking. But it was cool, it was cool.
Keith Cline (34:14)
Well, I want to talk about Impellent because I mean, because you became an operator, you did things after. But, you know, I do want to spend time talking about Impellent because obviously you guys are doing really meaningful work. So what led you and David kind of down the path of creating Impellent Ventures?
Phil Beauregard (34:31)
Yeah, so after, I don’t wanna lie over it super quickly, after Objective Logistics and Rekindle, I had this my blue period to a degree where I remember looking in the mirror and just essentially, and this is for the entrepreneurs out there, I was at a shape, I’d gone into it just kind of an athlete and in great shape and eating well and all that stuff. And then by the time I was done,
I was a shell of my former self as it pertained to mental and physical health. I can see it clearly now. I was an anxious wreck. And like overweight and red, drinking too much, like was, I was in a bad way. And so it took me a while to kind of get back to realizing that that was no way to live. Like fat, drunk, and stupid is no way to go through life son, right? So.
Keith Cline (35:27)
Mm-hmm.
Phil Beauregard (35:30)
After that, it was probably a good three years, I ended up doing some side stuff, some fun stuff, but then I ended up tacking on and I remember a couple people that we’ve mentioned ⁓ called me and said, hey, we have this company that could use your help. Do you think you could help them as an executive? And I just said no. They’re like, no way. I’m happy. Everybody leave me alone.
And then they asked a couple more times and there people I really cared about and I said, yeah, I’ll take a look at it.
And that started four years of three different gigs where I was just extremely successful as an executive, that I would get dropped in by the private equity and the boards. And it’s really when I kind of like became an adult and an operator and had an awesome run. I was naming my salaries and my equity plans and had a huge offer for the next one. And just at that point was like, I don’t think I want to jump from Lily pad to Lily pad anymore.
Keith Cline (36:13)
Mm-hmm.
Mm-hmm.
Phil Beauregard (36:29)
So what am going to do? I want to find something that’s a little bit more permanent. And I had some overtures from some of the larger firms about being a partner in venture. I think that I had a lot of friends and colleagues that were kind of always saying, hey, why don’t you think about that? I think you’d be pretty good at it. ⁓
And I said, all right, at that point I was like, again, once again, why join the Navy when you can be a pirate? I took that momentum and just said, all right, I’m going to go start my own firm. And I was doing a listening campaign and making a bunch of calls and saying, you know, two people that were running venture firms and just saying like, how did you do this? What do you think about this? ⁓ And I called David. He was one of the people. ⁓ And if you guys don’t know David, ⁓ David Brown is quite the opposite of me. He’s the end to my yang. Like David is very tall. He’s got great hair. ⁓ Great golfer. And I don’t know, a single person that has anything bad to say about him. I’m the opposite of those things. I’m not short, but I mean, I’m not like, you know, as tall as David is. ⁓ And so when I called him up, he called me back and was like, hey.
Keith Cline (37:19)
can’t.
Phil Beauregard (37:44)
Little did I know that he was going into his fund 2 and had his anchor who was repledging for a little bit of a larger amount. And ⁓ he said, why don’t, have you ever thought about joining forces? Because entrepreneurship, not entrepreneurship, entrepreneurial venture capital companies are lonely, just like anything else. And so, you know, I’ve been thinking about it combining forces or adding a partner. And so it was a little while after that, but we ended up having a lot of conversations around it, threw the kids into a pit, had the wives agree that this was a good idea, and then we burned the ships. So that was when Impellent started, or Impellent in the form that it is now.
Keith Cline (38:27)
Very.
Alright, so let’s talk about the firm and what you guys do.
Phil Beauregard (38:33)
We touched on it at the beginning, really, Impelling Ventures is a fund that was rooted in the concept of entrepreneurs outside of the hubs or entrepreneurs that are overlooked.
Instead of being heat seekers, we wanted to be truffle pigs. Instead of going just to San Francisco, we wanted to look at all these different places and we wanted to see the best deals and get the most deal flow we possibly could in a certain set of cities that weren’t San Francisco. ⁓ And then just…try to capitalize on those opportunities and get into them early. We wanted to be the first check-in. We wouldn’t mind if we did it with another firm or anything else along those lines and really just be like any other venture firm, the firm that these folks relied upon. But I think our ethos had a bunch of different points that…we really practiced and it’s hopefully up until this point become apparent amongst entrepreneurs, the ones that know us and ask about us, that we don’t give up on our losers, right? Like we, one, we can’t afford to. ⁓ We don’t think that, you know.
It’s just going to be one company that returns our entire fund every single time. We want to act like all of them will at all times and practice unconditional love as much as humanly possible or unconditional support to our entrepreneurs. And we’re human, so I’m sure sometimes that we can be a little bit.
pull down on some of that, but I think more often than not, we are a firm that comes in and just sticks by you through thick and thin because we know what it looks like and what it feels like. And we truly believe that extraordinary people can do extraordinary things if only given the time to do it. And so we just don’t know how big that’s gonna get. And we also think that any human being to this point in time right now in civilization that thinks they can predict what a market’s gonna look like or what a product or company and where they’re gonna end up in 10 to 15 years is totally crazy. So what do we bet on? We’re not betting on the product strategy or just a forecast or exactly where entrepreneurs think that all this stuff is gonna go. We’d rather learn about how they think and who those entrepreneurs are. Because, you know, this isn’t new, but we really practice the art and science of betting on people. And that’s turned out extraordinarily well for us so far. It’s only, you know, six years in for David, five years in for me, but we just, you know, got ⁓ representation by Cambridge Associates for our next vehicle, which is, you know, a rarefied air for us.
we’re doing pretty well. Well, our portfolio companies are, so they make us look good.
Keith Cline (41:44)
Well, some of the, mean, obviously there’s more portfolio companies than this, but the ones that kind of stood out to me are just entrepreneurs that I respect greatly, like EnFi with Scott Weller and Josh Summers, Grocers List with Ben Jabbawy like he’s awesome. ⁓ I guess an entrepreneur that I don’t know about a recent investment that when I saw their video, their explainer video, it was just so obvious, Gander Robotics.
Phil Beauregard (41:56)
Yeah.
Yeah, there’s such stories behind all of these by the way, like meaning like how we got the deals is just making me laugh a little bit because EnFi I knew Josh and Scott, Scott was an LP of our fund and he was like, we started a company, I’m like, fuck you. And it because I was like, okay, when? And I was like, can I give you money? And he was like, I think it’s all filled up by Unusual and Lars, I’m like, double fuck you. Like, what is your problem dude?
Keith Cline (42:27)
Hello?
Hahaha!
Phil Beauregard (42:40)
Like, you know,
what is your deal? And then he was like, maybe we can find you some space. And then he was like, we can’t find you some space. I’m just like, I’m never talking to you again. You’re lucky I don’t come to your house and do cold murder on you right now. ⁓ And we ended up being able to tuck into that one. So that was awesome. then Josh, Josh is extraordinary. mean, he’s great. They’re doing extremely well, by the way. They just topped up with an unbelievable strategic venture firm. ⁓
Keith Cline (42:50)
you
Yeah. Fintop, Fintop, right?
Phil Beauregard (43:08)
Cool, that’s a good one. And Fintop yeah. And then Ben, I mean Ben, like, Ben texted me and was like, I’m thinking about doing something. essentially I just wrote, yeah, I’m in, what do I send the check? And so he was like, well, don’t you want to hear it? I was like, no, I don’t care. We don’t care.
Keith Cline (43:32)
No brainer. Like what he did with privy was just, like that’s a boundary you want to back.
Phil Beauregard (43:36)
I had court-side seats to that one, man. Court-side seats, like, Ben is an extraordinary human being. I mean, to go from 100 plus employees down to two, and the shit that he went through, and then to bring that back up with the sale to Attentive was just like, how could you not bet on a guy like that, right? And then Gander, another one, by the way, that you didn’t mention, that’s probably faster than all, I mean, anybody right now is, Morrissey Market. Brad.
Keith Cline (44:08)
Really?
Yeah. Killing it?
Phil Beauregard (44:12)
I can’t even begin to explain to you how fast that company’s growing.
Keith Cline (44:15)
Wow, okay, I need to them on my podcast. I haven’t had them on yet.
Phil Beauregard (44:18)
Unbelievable. And you know what? Could not happen to a better group of people. That guy, Brad McNamara, he’s a great human being. The people that you mentioned are all great human beings. So that’s pretty cool. And talking about another great human being, I didn’t know Michael Ottery from Gander Robotics, but the way that we met them, by the way, we have such an enormously strong Boston presence.
Keith Cline (44:33)
Bye.
Phil Beauregard (44:47)
Like we were thinking, we were doing it the other day. We’re like, we are in on every Boston deal that like we think is it’s just, we continue to be, we’re back in Boston once a month. Like the only reason that I don’t live there is because of family. ⁓ you know, and my kids. Yeah.
Keith Cline (45:00)
Right, like me, I live outside of Philadelphia. And people are like, you’re not in Boston? So here we are, we have two people talking about the Boston Tech ecosystem that actually don’t reside there.
Phil Beauregard (45:10)
I think that’s the strength of what people have created there to a degree and how tight that community was and hopefully they can carry it into the future. ⁓ But Gander, I got a call from Bill Aulet and John Corey, boom, within a day of each other and say, this is a guy you gotta check out for various reasons.
Keith Cline (45:15)
Fact. Agreed.
Mm-hmm.
Phil Beauregard (45:31)
And so said, well, mean, if these two guys are calling. So I got on a call with him, didn’t know what he did. And I asked him the prototypical question of like, what’s the hardest thing you’ve ever been through in your life? And he essentially just, Michael just was like, you got 10 minutes? And I was like, this is gonna be something. And by the way, I’ll usually tell entrepreneurs like what my things are, not for the sake of comparison, but to be vulnerable. Cause I mean, they’re pretty shitty, right? Like in that way, they’re like, my God, he’s willing to talk about that. ⁓
Keith Cline (45:55)
Mm-hmm.
Phil Beauregard (46:01)
So Michael, and he doesn’t mind me sharing this obviously, otherwise I wouldn’t, was born to a single mother with three siblings that were different fathers. ⁓ He was homeless up until the point where he moved in with his alcoholic father who’s now incarcerated for what he didn’t specify but said it’s the worst thing you can possibly imagine. ⁓ And dropped out of college, got kicked out of college.
Keith Cline (46:06)
Mm-hmm.
Phil Beauregard (46:30)
and was just kind of at Wits End after a couple months of school, and was at Wits End Community College. And he signed up for the Navy. He was like, need structure. Like, this is either gonna save my life or I’m gonna die. And so Michael ended up, flash forward, I mean obviously there’s a lot in between there, but he’s a naval commander. ⁓
You know, he graduated with dual engineering degrees and he’s currently at MIT, obviously, like, just finishing up his MBA. And he created a submersible, a carryable submersible, or is creating, that you can drop off the side of a ship, a naval ship, but also a cruise ship, that uses modern, you know, technology, AI and sonar to…
Keith Cline (47:02)
Mm-hmm.
Phil Beauregard (47:22)
pinpoint where a man overboard is, or object overboard in the water far better than anything that’s ever been invented before. It deploys a life-saving device and a player. And so it’s just like he made something that’s non-kinetic kind of defense technology ⁓ that you know, is going to save a lot of lives. And that’s what they’re working on now. we, alongside Underscore, just were like another one of those, you know, okay, what, where do I sign.
Keith Cline (47:54)
Right, yeah, like when I saw the video, like, and I saw the two founders backgrounds, I’m like, oh, this is a winner. like, all of sudden, it’s like, this is the first use case for this technology. It’s just gonna be like, I bet you massive other things to think about. So, all right.
Phil Beauregard (48:08)
Yeah, and Michael will admit to himself that there’s a lot between idea and where it goes, right? So execution is 99 % of the game. So we’ll see.
Keith Cline (48:20)
Well, we need to talk about your partner, of course. ⁓ So here’s a courtesy of LinkedIn. Someone shared this for all you, I think. ⁓ So ⁓ your partner is what most people know him as his Black Thought of The Roots. So how did that come together?
Phil Beauregard (48:40)
Yeah, you’re sitting outside of Philly right? So Tariq is like a brother to me. He’s been a good friend of mine, a dear friend for a long time now. It all started when Twitter or X to me had utility and I slid into his DMs. This is in like 2014. And just to say, I mean, I was a huge fan of The Roots.
Keith Cline (48:42)
Yeah.
Phil Beauregard (49:05)
and Tariq’s intellect and kind of like what they were doing there. were so, the longevity and everything else like that. I mean, that was like a company, not just a band. And ⁓ yeah, I never in a years did think he was gonna respond, but I said, hey, would you come to Harvard and come speak to the students at the iLab for part of a series? And he ended up saying yes. So he came, ⁓ he gave this talk. ⁓ Dennis Keohane was the interviewer. Yeah, yeah, yeah.
Keith Cline (49:33)
tennis was? Really?
Phil Beauregard (49:35)
And he did a great job. But Dennis asked him a question that I explicitly told Dennis not to ask. And that was, don’t ask him to rap. And Dennis was like, Dennis fucking asked me to
Keith Cline (49:48)
I have to ask him to rap.
Phil Beauregard (49:50)
little shit, ⁓ but it ended up being like he dropped, was right before FUN Master Flex, was Tariq’s first viral online moment, like he dropped this crazy awesome freestyle in front of, in a Harvard Letterman sweater, in front of all these Harvard students and people that got invited into the room. It was just nuts, like standing like crazy. ⁓
Just fire. And Rich Miner was there and Jen Lum. And me, Rich, and Tariq ended up just hanging that entire night and became friends. It evolved from there. when I was joining, and Tariq was making angel investments, right? Like he was seeing Nas and Jay-Z and stuff like that. And so when we were raising for our first vehicle together at Impellent.
I was like, yeah, Dave, let’s go to New York and wouldn’t it be great to have Tariq and Amir Quest and Jimmy and Dave Chappelle and Manuel Miranda be investors in our fund? That’s cool, right? And the answer is obviously yes. And when we sat down with Tariq for dinner,
Keith Cline (50:55)
Wait, all those people are investors in your fund?
Phil Beauregard (50:57)
No, we didn’t end up getting all of them. They, they, unfortunately, a bunch of Goldman Sachs bankers, you know, said, said, stay away from these guys back then, back then. And they were wrong. ⁓ But no, I mean, we got, we, got a couple of them. And so, yeah, we ended up, we ended up saying, making the overture to Tariq and he just said, yeah, he said like, but I I’d also like to be a partner at Impellent Ventures. And we were like,
Keith Cline (51:00)
Okay.
Phil Beauregard (51:26)
well that’s a different conversation entirely Tariq, clear your schedule, right? And so that’s how it came to be, was a lot of conversations again, know, fools rushing in. And yeah, Tariq’s a GP and he’s amazing, he brings a completely different perspective. But he’s also still on The Fallon Show and stuff, so. He’s got, guy’s got a lot going on.
Keith Cline (51:50)
which is why you get the luxury of having like an LP meeting where we get to go to the backstage of the Fallon show and so and I look at this picture I’m just like I know like least half of these people. I’m like this is awesome.
Phil Beauregard (51:56)
I will see you.
Yeah, 30 Rock is like our third office. It’s actually super cool. Like you just like sit in the hall. I remember one day I was sitting there and I don’t really get whatever. I’m amazed by and feel a little bit skittish around my wife and not celebrities, right? ⁓ But standing there, I remember one day.
I see this wisp of white hair and a guy asked me where the bathroom is. I’m tucked out of Tariq’s dressing room and that’s Steve Martin. I… Yeah, and it’s funny. He was like, hey, he was like, hey, do you remember where the bathroom is? And I said, yeah, it’s down to the hall to the left. I’m like, oh my God, like my dad, three of me. And he actually dropped a line on me. He was like, oh yeah, he’s like, I haven’t been here for 30 years, right? And I’m just like fucking Steve Martin.
Keith Cline (52:30)
Asking you where the bathroom is.
That’s awesome.
Phil Beauregard (52:52)
That was
That was cool. We saw Jayson Tatum riding through the championship and like that sort of stuff. But yeah, to tell you the truth, I’d rather be spending time with my wife and kids, but that was cool.
Keith Cline (53:03)
that, but it’s still a nice little perk. right, obviously AI is everywhere and I always like to ask the podcast guests, know, like how are you incorporating into your workflow, your day, your personal business? Like just kind of like open-ended question.
Phil Beauregard (53:18)
I’m currently using it right now for, like everybody else, I have an executive briefing tool that essentially just gives me my, in the morning it wakes me up with my coffee, that just gives me an entire analysis of my day tells me who I’m meeting with, what they are to me. ⁓ It even gives, ⁓ for certain types of people, it gives me a ocean analysis of their personality. What our last, kind of CRM-ish type stuff, but just take general takeaways and then I can expand into them on my Google Drive because it spits it out there as well and go in and just kind of have a bigger dossier that lives there. then Granola kind of does all that stuff to me.
So there’s a lot of those things. ⁓ And then I also have a relationship intelligence system, which is essentially a skill or agent that tells me where my relationship stands with anybody and what the ledger looks like. Cause I always want to know if I’m taking more than I’m giving. And I think one of the things about Boston was always like, there was this huge, like, everybody used to talk about pay it forward a lot.
Remember back like Matt Lauzon and like Balter and Sarah Hodges, know, the tech prom Mike Troiano Everybody would just kind of that phrase, pay it forward. ⁓ Scott Kirsner ⁓ And so that was, that’s something that stuck with me for a long time is that like, I, I’ll always tell my kids and also just like other entrepreneurs, like put plant seeds, whether or not you’re to come back to that part of the forest. Cause you just never know. Right. And so.
Keith Cline (54:33)
Yeah, totally.
yeah.
Phil Beauregard (54:59)
We try to do that. We try to pay it forward as much as humanly possible. ⁓ So that’s my relationship intelligence system. And then we have, ⁓ you know, some other kind of stealthy internal tools that help us with our decisions and days. So we have a lot of agents spun up to the point where we’re not going to hire an associate. ⁓ Not yet. Yeah. The only reason we would hire an associate in the future or associates would be because we don’t want to go to dinners anymore. We don’t want to go to events. Our livers are well, are over experienced, over taxed. And, know, there’s only so many bourbons that a human body can take over a lifetime. So rather export that to the young ones.
Keith Cline (55:29)
Your job is to go to these dinners.
Ha
All right, one more question. ⁓ So on your LinkedIn, you have founding advisor at Toast and Shield AI. Like how did you become a founding advisor? Like obviously everyone knows Toast and the success that company has been, but Shield AI is a massive success too.
Phil Beauregard (56:08)
Yeah, so toast is an easy one, right? Like Steve Papa’s a close friend, or anybody that can call Steve a friend. ⁓ And yeah, Steve’s a close friend of mine. And Steve, back in the day, knew we were creating restaurant technology, so we helped those guys out in the beginning. ⁓
and Steve and Aman obviously, they were amazing guys. And the funniest part of that, I gave a lot of good advice ⁓ and helped them out a lot. But there’s one thing that’s the funniest part of it. And this is really early, by the way, once they, I mean, they obviously became massive and like, know, toast went like this. so, but I remember we were sitting there and it’s fucking documented.
I gave the one worst piece of advice ever. And that was, they were originally building a check splitting app on mobile, like literally like you and a friend go out and like split the check and we’re done. And they just realized how shitty POS systems were.
Like from like a build standpoint, how archaic and innovators dilemma. And that was when micros is moving to the cloud and like, blah, blah. We were so in depth in the POS world. And Amon was like, we’re going to rebuild the POS. That’s what we’re going to do. We’re not going to do this stuff. I because it’s so bad. And I was like, don’t do it.
Keith Cline (57:36)
do it man, don’t do it. Well you gotta Oracle owns micros at that point, right? you gotta go take on Oracle, okay.
Phil Beauregard (57:40)
I literally, come on Keith, you and can’t justify that advice.
Keith Cline (57:46)
No,
I mean, granted he had the guts to go do it because I mean, it’s just like that was such a legacy software that you had to rip out of these restaurants to replace it with the cloud, which it makes sense now, but hindsight, right?
Phil Beauregard (58:01)
And they taught me a very, very valuable lesson. Do not. Yeah, and also just like when somebody’s amazing, of course they’re gonna reinvent the fucking future. ⁓
Keith Cline (58:08)
Yeah, disruption, disruption.
Phil Beauregard (58:17)
And so that was toast and still very close with those guys to this day. Played golf with them on very recently actually. And then, I’m terrible at golf by the way. so anyway, then Shield AI, I met those guys at the Harvard iLab and Brendan. And it was when there were three people. You know, a guy from Lincoln Labs and, I mean, Brandon and his brother Ryan. And Brandon was this guy that walks up to me and I’m talking to him. And if you ever meet Brandon, Brandon’s like this good looking, like in great shape guy who’s like telling me his background. And he’s like, yeah, I was a Navy SEAL captain. I’ve done four deployments. He looks like he’s like 15, except jacked. And he’s like, yeah, Stanford and Harvard or whatever.
Keith Cline (59:09)
Right?
Phil Beauregard (59:14)
I’m just like, I hate you already. ⁓ I don’t like to cover your jib. Get out of my face, you perfect human being. And Brandon was talking about these search and rescue drones. And so I was like, these guys are amazing. I ended up introducing them to Founder Collective early on to Andreessen. I have all the emails that I sent them all out.
Keith Cline (59:38)
Wow, you made those intros, wow.
Phil Beauregard (59:40)
Well, so, so no, but Andreessen said, no, they were like, we don’t do defense technology. Yeah. Until they invent Ben’s really funny because like I, every time that I send a deal, I actually have to send another deal to Ben right now that I really think that like, but I will append one of my companies, like meaning there was DraftKings, there was this, they’re like, sent these companies all to Ben, to, to, these guys and I’ll append one of the emails where they said no to it.
Keith Cline (59:44)
They did? Okay.
Phil Beauregard (1:00:07)
And she’ll ask one. I’ll be like, I got another one for you. Here you go. Right. And there’s like six, usually six unicorns in there, dekakorns. ⁓ And so, and so it’s really funny. And I started to Accel and Sequoia and all these things like.
Keith Cline (1:00:11)
Right. This one went public. this.
Ha ha ha.
Phil Beauregard (1:00:24)
Andresseen ended up doing it at the B and I kind of ribbed Scott Cooper a little bit about it. was like, hey man, I was like, you did it. You rebranded Defense Through American Dynamism. Like good for you. Like, you know, that’s cool. And he ended up being like, yeah, we did it. We’re really excited about it. I was like, well, you could have gotten at it at 4 million posts. And he was like, he was like, know, he like, he essentially said it was just like, we’re writing $15 million checks, man. can’t, like, it was.
Keith Cline (1:00:43)
Wow.
Phil Beauregard (1:00:51)
we’re cool with where it’s at now. Right? And I was like, there’s the law.
Keith Cline (1:00:53)
We’re good. We’re happy.
But David Frankel’s
pretty happy too, right?
Phil Beauregard (1:01:00)
Frankles, I don’t like I don’t I want to bottle those guys like I I don’t I have a very high opinion of myself and what we’re gonna do here but like you keep seeing these new things you’re just like dude how do you guys do it like you know Coupang and then SeatGeek and TradeDesk and Uber and WHOOP and and and Suno like these guys are just ridiculous
Keith Cline (1:01:16)
amazing.
Uber, Uber.
Pillpack, PillPack PillPack’s like like a.
Phil Beauregard (1:01:29)
PillPack’s another one that I helped out a lot.
Keith Cline (1:01:34)
Yeah, that was like, well TJ was kind of around Sloan and he met Elliot at Sloan, Yeah.
Phil Beauregard (1:01:38)
I was very close. So… I didn’t know Elliott, but TJ, they’re another one of my famous anti-portfolio companies because I remember TJ was like, you want to invest? And I was like, well, I didn’t have any money. That’s why I didn’t. But I was like, they’re founder issues here. Because they were getting rid of their third co-founder, was like, I don’t know.
Keith Cline (1:01:51)
No.
Okay, alright, alright,
Phil Beauregard (1:02:03)
TJ’s a dirty hippie and like, know, so on and so forth. you know, I’m just ribbing him. He’s amazing guy.
Keith Cline (1:02:09)
Well, the crazy thing about that company, my dad, so I grew up in Hooksett, New Hampshire, which is right next to Manchester. My dad’s company, had a leather coat factory when I was growing up in that same mill yard that PillPak was in, the Amoskeag Millyard. Yeah, just random.
Phil Beauregard (1:02:23)
Really? Leather coat fashion?
So were you like six years old wearing leather coats? You must look awesome.
Keith Cline (1:02:30)
I had the replica of the Michael Jackson thriller coat. I was all in. ⁓ But you know what it taught me though? Hard work, because I had to go clean the factory every Sunday while my friends were playing. I was picking up leather scraps, cleaning bathrooms, you know, like it was like a badge of my brother, then my sister, then me. Is that what’s wrong with me? Now it makes sense, totally. So anyways.
Phil Beauregard (1:02:35)
means a lot.
Oof.
Probably have, probably get chronic bronchitis nowadays or something like that from that, right?
this.
Keith Cline (1:02:57)
Well Phil, I could talk to you forever about stories, but I guess I gotta cut it because people will be like, my God, they just keep talking. Well thank you so much for…
Phil Beauregard (1:03:04)
Now let’s go create some more, man. Like we gotta go create more stories. I’m done with those. I wanna go create more of them. So everybody that has an awesome company, come my way. If you wanna venture capitalists that swears a lot and we’ll get into fist fights for you, I’m your guy. Just joking.
Keith Cline (1:03:07)
We need a part two with like, you know, so… ⁓ my god, there’s so many others to talk about.
Yes.
All right, well, Philip,
thanks so much for taking the time to walk us through your background story, obviously the great advice, and obviously all the great stories.
Phil Beauregard (1:03:29)
Yeah, and by the way, one thing that I do want to cap it off with is that everything that we’ve talked about here is a hindsight type thing and it all sounds very Instagramy. There’s a filter over all this stuff when people talk about themselves. ⁓ So all of that stuff up until now was a hell of a lot harder than it sounds, or at least I depicted it. And not as smooth too, but you have a funny way of kind of looking back at things with a little bit of romanticism and I can’t.
Just keep going. It’s awesome. Life is awesome. All right, brother.
Keith Cline (1:04:01)
That’s a fact.